The Flaw in the Design
by naughty-grrrrl
Summary: Samantha's journey into who she wants to be, both inside and out, and how it changes the Winchester family irrevocably. Part of the Good-Girls!Verse, the sequel/prequel "Good Girls Do…" is set in the middle of Part 4 of this story.
1. Part One

**Title:** The Flaw in the Design  
><strong>Author:<strong> Naughty_grrrrl  
><strong>Artist:<strong> Asmadaima  
><strong>Fandom:<strong> Supernatural  
><strong>Genre:<strong> Romance, semi-AU  
><strong>CharactersPairing:** Dean/Sam(antha), John  
><strong>Rating:<strong> NC-17  
><strong>Wordcount:<strong> 15,195  
><strong>Spoilers:<strong> Set pre-series.  
><strong>KinksWarnings:** Explicit M/M sex, AU, underage wincest (beginning with Samantha at age 14, but without actual penetration until age 16), feminization, transexual!Sam, transgender issues, body modification, bottom!Samantha, crossdressing, first-time, schmoop, domestic!fic, angst.  
><strong>Summary:<strong> Samantha's journey into who she wants to be, both inside and out, and how it changes the Winchester family irrevocably. Part of the Good-Girls!Verse, the sequel/prequel "Good Girls Do…" is set in the middle of Part 4 of this story.  
><strong>Disclaimer:<strong> I do not own Supernatural, nor the characters portrayed in this story and I make no profit from these writings.

**Author's Note:** This was written for the first ever Spn_Kinky_Bang and I am very proud to present to you all. I am unfamiliar with transgender issues and the process of changing genders, i.e. hormone therapy, surgery and their effects on a male body, so I have done as much research as I could and deduced the rest. So don't take this as gospel truth. ;p

I'd like to thank **Emeraldheiress** for beta services without which this story would have been riddled with misspellings and grammar errors. Also, thank you to **Asmadaima** for the wonderful art for the story. The way **Asmadaima** drew Samantha is just perfection, so wonderfully vulnerable, just the way I saw her in my mind! If you would like to see the art **Asmadaima**created, go to the addresses below.

http :/pics .livejournal. com/ naughty_grrrrl /pic/ 000010dh

http :/pics .livejournal. com/ naughty_grrrrl /pic/ 00006t8q

http :/pics .livejournal. com/ naughty_grrrrl /pic/ 00007kkx

* * *

><p>It started when Sam was a little boy; he always felt… different. At first he couldn't say why. It was just this deep feeling like he wasn't the way he should be, the way he thought of himself in his mind. He never wanted to do the things other little boys did. Things like playing with their Tonka trucks and army men, getting messy in the dirt while building forts and thinking up ways to win the playground war. For Sam, being <em>one of the boys<em> had never fit the mold he had for his own life, at least not the one he envisioned in his mind.

One day, when Sam was eight and feeling especially uncomfortable on the playground with the other kids, Dean made a joke about Sammy being a girl. He'd laughed and said they should call him Samantha from now on, because he might as well be a girl. All the other kids laughed and went on playing, but for Sam, as soon as the words were spoken, he knew it was true. It was as if a spotlight had been shined into the confused darkness of his mind and Sam instantly understood after so long why he felt _wrong_. He _was_ a girl, even if his body said otherwise.

Once that revelation came, Samantha was like a new person. Same thoughts, same body, but from then on she saw the world from the viewpoint of a girl. No matter what the rest of the world chose to see her as, she knew the truth and that was all that mattered.

For years Samantha only admitted this revelation to herself, worried about what her father and brother… especially her brother… would think about it all. In her mind she referred to herself as a girl; she considered herself a girl who just happened to have some extra parts on her body.

As she got older, Samantha got creative with how she presented herself to the world. She still wore jeans and t-shirts like every other boy, but underneath she let her inner girl flourish. Whenever she was able to, pocketing change and forgotten money from her family, she would find moments to go and buy frilly little girl panties and bras. Shades of pink and purple, yellow and red; girly underwear with cute little bows and hearts and anything else that caught her fancy.

However, she had always known that one day her brother and father would find out, that she wouldn't be able to keep it to herself forever… that she wouldn't want to, either.

* * *

><p>It was a few months after Samantha turned thirteen, when Dean discovered her secret.<p>

The day had been like any other day, walking home from school with her brother, laughing and joking about some random thing. Their father was away, like always, on an extended hunt that had kept him away for weeks already and was looking to be even longer. The cold rain started falling from the sky, soaking them through in a matter of minutes. Dean and Samantha had run home, trying to get warm and dry before catching a cold.

Slipping into the small house they were living at, Dean started pulling his clothes from his body, shivering as he moved, "Sammy, get undressed, dude. It's freezing in here, stupid heater kicked the bucket again, and you need to get warm."

Samantha nodded her head and started to walk towards the bathroom, bottom lip between her teeth as she worried it.

"Sammy, what'd ya doin'? You're gonna track water through the house. Change here."

By then Dean had stripped down to his boxers, hands on his hips as he frowned at Samantha.

"Um… I need to go to the bathroom." Samantha said quietly, trying again to pass by Dean.

"So get your clothes off and go. I'll put them in with a load of laundry."

"I… I'll change when I get to the bathroom."

"Gooddammit, Sammy, why do ya gotta be so difficult." Dean huffed as he leaned over and, before Samantha could jump back, whipped her shirt over her head.

Dean's eyes got impossibly wide as he took in the pale pink, lacy training bra Samantha had on, mouth moving, but no words came out.

Samantha tried to cover herself up, but Dean's hands pushed them away after a few moments and he finally spoke. "Dude… why are you wearing a bra?"

"I don't want to talk about it!" Samantha cried and ran to their room, the door slamming and locking after her.

Leaning back against the door, Samantha could feel tears on her cheeks and she wiped them roughly with her hands, a sob falling from her lips. She stood there for a few minutes trying to get her emotions under control before pulling off her jeans, her hands trembling as they jerkily tugged the material down her legs. Taking a deep breath to try and calm herself, Samantha walked over to the old scuffed and chipped dresser that came with the house and pulled a new outfit out of it.

The sound of the door knob turning made her look; a few seconds later Dean was standing in the open doorway with his lock picking set in his hands. "Knew you would lock it, I swear you're such a girl, Samantha."

Another sob escaped Samantha at her brother's oblivious words and she held her clothes in front of her body.

"Sammy, why are you wearing girls' panties and a bra?" Dean asked quietly as he took a step closer.

Samantha shook her head, tears falling even more as she tried to figure out a way that this wouldn't end up blowing up in her face.

"Sammy," Dean walked up to her and cupped her cheeks, his thumbs wiping away the tear tracks on her cheeks. "Tell me, I won't be mad, I promise."

She stood there quietly for a few seconds and then whispered, "I'm a girl… I feel like a girl inside… I just wanted to feel like one on the outside, too."

"You want to be a girl?" Dean's faced pulled into a confused frown as he looked at her.

"No, I _am_ a girl… at least in my mind. I don't _care_ what everyone else thinks, I'm a _girl!"_ Sucking in a deep breath, Samantha calmed herself down. "I just wanted to be able to dress like I feel inside."

"Okay, Sam-"

"I want to be called Samantha."

They stood there for a few quiet seconds as Dean absorbed Samantha's words, his face going through a hundred different emotions before finally the trademark Dean Winchester smirk appeared, even if it was a little less bright than usual, and he laughed softly. "I always knew you were a girl!"

* * *

><p>From the moment that Dean found out about Samantha's secret, Dean slowly adjusted to the idea that his little brother Sam was now his little sister Samantha. It wasn't perfect, but they grew closer than ever as Samantha became more comfortable with who she was and what she wanted. Dean started buying her clothes and such here and there, his way of showing he was okay with Sam now being Samantha.<p>

The first was a pair of dainty little ballet slippers that Samantha had sighed over through a store window, eyes all dreamy and wistful as she look at those perfect little things, before Dean dragged her towards the grocery store with a knowing smirk on his face. Then it had been a girl's fitted sweater, a denim knee length skirt, a frilly scarf, jewelry, and a few things of basic make up. Before long she quickly amassed a small treasure trove of "girly things", as Dean like to call it, and she jumped at the chance to be the girl she felt like on the inside.

On days when it was just them, when they knew their father wouldn't be home anytime soon, Samantha let herself dress completely like the girl she was in her heart. Dean would laugh and give her this small little smile that lit up his eyes whenever she would prance around the house feeling happy and whole for the first time in her life.

"What do you think Dad would say if he knew I dressed like this when he's gone?" Samantha asked quietly one night as they watched TV.

They were cuddled together on the couch, Samantha pressed up against Dean's side with her legs tucked under her and her head resting on Dean's chest. She had on a pair of pink daisy-duke shorts and a white fitted tank top and matching pink hoody... the outfit was a gift from Dean for her fourteenth birthday a few weeks ago and had quickly become her go-to comfy clothes when she needed to feel comfortable, but "girly" at the same time.

She'd let her hair grow out longer, not as long as she'd like it to be, but it was to her shoulders, a messy choppy cut that let her pretend to be the boy in public and a girl in private.

It had been nine months since Dean had found out about her and recently Samantha had finally found the courage to go to the library and read up on transgender issues where she found some interesting things. Because she had realized who she was at a young age, she had a number of options that older transgendered people didn't. Samantha hadn't hit puberty yet, so her body was still in a sort of holding pattern before her testes dropped and her voice lowered and she started to grow hair, thin out and grow taller; before her muscles and bones took the shape of the man she could have been. If she wanted to, she could start taking hormones to grow breasts, keep hair from sprouting in unsightly places, redistribute fat more appropriate for a woman, and keep herself from becoming as tall as she believed she would eventually grow.

It was her chance to be a woman on the outside as well as inside… but she wouldn't be able to do any of that without their dad knowing. It would be obvious before long.

"I don't know, Sammy," Dean shrugged and pulled her closer to him, pressing a kiss to her temple. "Dad's a little hard to figure out, sometimes he takes news better than I imagine, other times… well, it's not so great."

After nearly a year, Samantha had realized that no matter how much she tried to make him call her Samantha it just didn't work. But she had at least got him to stop calling her Sam. Sam was the little boy she used to be, Samantha was the woman she wanted to be and Sammy, well, Sammy was Dean's little sister who used to be his little brother.

"Do you think he would be able to accept me as a girl?"

Dean turned towards her and threaded his fingers through hers, their palms flat together as they looked into each other's eyes. "Maybe… why are you asking?"

"I want to start dressing like a girl all the time; I want everyone to treat me like a girl." Samantha nibbled on her bottom lip nervously. "I was reading at the library yesterday that I could take hormones to help me grow breasts and to keep from growing heavy, coarse hair in places. My voice wouldn't lower and I wouldn't get too tall for the average girl… stuff like that."

"Aren't you too young, Sammy?"

"Well, most transgendered people don't start the change until later in life, but that's usually because they haven't publically acknowledged who they are inside or they were kept from making the change. They're have been people who have done it early… it helps the transition to be easier if the hormone therapy starts before I hit puberty. After that there are some things that couldn't be changed or that would only be able to be changed so much."

"And you want to do it… I mean, become a women outside?"

"Yeah," Samantha gave him a little grin, "I wear bras even though I don't really need them… I want to have breasts and hips, curves like a real woman."

Dean swallowed heavily at her words and unconsciously adjusted himself. Samantha wasn't blind, she'd seen the way Dean had begun to react to her, especially in her girl clothes. Something had started to build between them a long time ago, even before Dean had found out about Samantha, and as they grew older it started to show more and more.

Maybe it was the fact that they lived out of each other's pockets or that they really didn't have anyone else except each other. She knew their relationship probably wasn't what most people would consider normal, even without the hunting life involved. They weren't like others siblings, fighting and hating each other, wanting as much space as they could get. Samantha and Dean were the opposite and always had been, but it was the fact that they were so different that allowed them to connect and depend on each other, each taking up with a personal strength when the other stumbled and fell. They were each other's strength and the last sentry against the harshness of the rest of the world.

As children they would cry and whine being parted from each other, holding tight to each other in their bed at night, their father's gruff voice cursing at the way they'd only cling to each other tighter when he tried to make them sleep in their own beds at night. It had never felt right being away from Dean for very long, even in sleep; Samantha missed her brother horribly when he went on long hunts with their father every so often. She missed him like a missing limb or a piece of her heart. He was a vital part of her life that she couldn't live without, he was her breathe and her life, her everything.

Even if he wasn't the person she trusted most in the world, there was a physical need attached to her love for him. Dean was attractive, she had always known that, but as she got older she began to consciously see it when she looked at him. He was tall, already 5' 11'' and bound to grow taller. He'd gained muscle over the years of helping their father on hunts and he filled out his clothes nicely. Dean always had a cocky grin or a dazzling smile; he made the female, and parts of the male population, wherever he went take notice of him without really even trying. But, that was only a small part of what made Dean, Dean. He was smart, no matter how much others thought otherwise, and gentle, kind… He was could always make Samantha smile whenever she was down. Dean took care of her, loved her, more than anyone else in the world. He was her brother, her friend, the boy she loved.

When she looked at Dean, Samantha would get a tingling feeling in her belly and she would feel out of breath and hot. She wanted him to hold her and kiss her and touch her, and wanted to do the same to him. She knew he felt the same way; she saw the looks he gave her when he thought she wasn't looking, the longing on his face. They both wanted each other, but hadn't taken the final step from "harmless" cuddling and tactile interaction, to something more… yet, but maybe now was the time to acknowledge what had been building between them for years now.

Taking a chance, Samantha crawled onto Dean's lap, keeping her eyes on Dean the whole time to make sure it was okay, as she straddled his lap and sat down on his upper thighs. Gingerly wrapping her arms around his neck and threading her fingers through the hair at the nape of his head, Samantha looked up at Dean and gave him a shy smile. "I want to be a girl, Dean, I want be _your_ girl."

Dean sat there looking like a deer-in-the-headlights for a few minutes before he blinked and pushed out the breath he'd been holding. With a gulp, Dean cautiously wrapped his arms around her, his hands cupping the soft plump flesh of her ass. "You _are_ my girl, Sammy, always will be."

Giggling, Samantha leaned closer and pressed her lips to his for a kiss. It was soft and sweet, innocently chaste, but with the promise of something more. Leaning back, Samantha licked her lips, giving Dean a teasing smirk when he groaned, his eyes locked on the way her tongue slid across the fullness of her bottom lip.

The second kiss was all Dean. He gripped his hands tighter on her ass, pulling her as close as he could as he leaned down and pressed his lips to Samantha's. He gently coaxed them open, groaning at the shy flick of Samantha's tongue against his. Dean pushed his tongue inside her mouth, rubbing the tip against Samantha's in a slow undulation that she quickly mimicked.

Several minutes later, Samantha came up for air, wiggling her hips slightly to put her feet in a better position. She stopped when a loud gasp escaped Dean's lips. "What? Did I do something wrong?"

Dean shook his head. "No, Sammy… it just feels really good with you sitting on my lap."

Samantha frowned for a moment as to why he would gasp like that and then like a light bulb, it came to her. Something was poking her bottom, had been for a while, but she hadn't paid any attention to it until now.

Blushing, Samantha purposely wiggled her bottom again, giggling evilly as Dean gasped once more. "Oops."

"Oops, Sammy?" Dean gave Samantha a mock scowl and then proceeded to tickle her where he knew she was most sensitive.

Crying out, Samantha tried to get off her brother's lap as he attacked her sides, but Dean had always been so much stronger than her. "Noooo!" Laughing through her cries, she dived off of Dean's lap and scrambled across the couch toward safety.

"Not a chance, Sammy." Dean pulled her back on to his lap, this time with her back against his chest. "Got you now."

Tears fell from Samantha's eyes as she laughed, trying to get away from his evil tickling hands. Grabbing Dean's hands as best she could, Samantha pulled them away from her sides and up onto her chest where she held them tight against her. Dean chuckled and let his hands relax finally, his warm breath gusting along the back of Samantha's neck.

Pressing back against her brother, Samantha threaded her fingers through Dean's, sighing as his much larger hands cradled hers. Dean nuzzled her neck and pressed a soft kiss behind her ear, whispering "Love you, Sammy."

"I love you too, Dean."

They stayed there for what felt like hours that night, just holding each other and talking, finally able to share their feelings for each other. They didn't take it any farther; neither was ready for that yet, but someday, they would be.

* * *

><p>Samantha had imagined a million different scenarios on how she would tell her father that she was a girl instead of the boy, that wanted to change her body to reflect that, but whenever she attempted to even broach the subject with him she inevitably chickened out. She was afraid of what he might say or do, of the fact that she worried that he wouldn't be able to accept her for who she is and would tell her to leave and never come back. The fear only grew bigger at the thought of him finding out about her and Dean as well. Her father and she had never seen eye to eye on a lot of things and she worried that that fact would only make things worse.<p>

The elder Winchester was completely entrenched in the hunting lifestyle and expected Dean and her to toe the line and be good little soldiers who followed orders without question. They bounced around from state to state, year after year, Samantha would spend a month or two in one school only to get shifted to the next and spend just as little time at that one as well. She valued her education and longed for a stable environment and a single place to call home… and she wasn't shy about voicing her needs. They fought so much, Dean always in the middle, trying to keep the peace as they railed against each for hurts done against the other.

It was that image she always saw when she thought about telling him. No matter how much she wanted to live freely as a girl her fear always kept her from taking the next step to closer to reaching that goal; her father's imposing scowl always stopping her at the last second.

When John Winchester finally found out about Samantha, it was by mistake. Her father had left that afternoon on a hunt that was likely to take a while and, as always, she excitedly took advantage of her father's absence to dress the way she wanted to.

She'd put on a cute little denim mini skirt and one of Dean's old metal band shirts that had shrunk a few sizes in the wash. Samantha had styled her hair and put on a dab of make-up; nothing too overdone, just enough to feel like herself again after a week of being stuck in boys clothes without a break. After changing, she'd gone into the kitchen and started dinner for the two of them, humming away as she worked.

Dean was getting off work soon; he'd been working at the local repair shop in town as a mechanic since he'd graduated high school the month before and Samantha liked to have dinner on the table for him after a long day of work. She liked the feeling she always got when she cooked for Dean, waiting patiently for him to get off work so they could sit down and enjoy their dinner together, snuggling up on the couch afterwards. It left a warm fuzzy happy feeling in her chest… the idea that they were married and living a good life together. Sure, the fact that they were siblings meant that that dream may not the "normal" apple pie life that most people had, but would be a happy one nonetheless.

Somewhere between the last year or two, Dean had become not just a boy but a man, and the image of him always seemed to inspire those fantasies for Samantha… of them finally having a place to call home and a steady life, free of the harshness of a life on the road.

At 6' 1", he was tall and muscled from training and hunting, his body finely tuned into a work of art that made everyone take notice. The sight of him in his dirty coveralls after a long day at work always made her blush and squirm, something about how much of a man he looked in them made her weak in the knees.

"Who the hell are you?"

Samantha screamed and whipped around at the sound of her father's voice, her heart jumping nearly out of her chest as he scared her. A second later she remembered what she was wearing as her father's eyes widen as he took in Samantha in her short skirt, makeup and fitted tee. _**'Oh god, this is gonna be bad,'**_ Samantha thought as she braced herself as her father started to yell.

"SAM?" His eyes bulged and his face pulled tight, his hands clenched at his sides. "What the hell is wrong with you, boy, why are you wearing girls' clothes? And is that _makeup_?"

"I-," her throat closed up around the words she wanted to say, needed to say.

"Goddammit, I knew something was up, but this?" Her father paced back and forth across the kitchen tiles, running his hands roughly through his hair in a move she'd seen him do a thousand times when he was pissed. "Well, explain yourself… now!"

"I," God, why couldn't she talk? "I… I want to be a girl!"

There, she finally said the words that had been on the tip of her tongue for years now. The weight of those words felt like the weight of the heavens on Atlas' shoulders, a burden that she forever wanted to be free of.

"Since… since I was little I knew I was different, but I, I couldn't explain why. When I got older I realized that I didn't feel like a boy even if that was the body I was born in… I felt like a girl." Samantha's quiet voice stuttered through the words, the whisper was like a scream in the silence of the kitchen. "I started dressing like a girl a while ago when you aren't home… it's the only time when I feel like myself."

Biting her lip, Samantha nervously tangled and untangled her fingers together, as she waited for her father to say something. A wet drop fell on her cheeks and she wiped it away with a jerk of her hand. She was crying, '_**Great, that will just piss him off even more.'**_

"You want to be a girl… wait a minute, you said when _I'm_ not here, Dean knows about this shit and didn't report it to me?"

"I've known for about a year now, Dad." Dean said through gritted teeth as he stepped into the house through the backdoor, dumping his lunch pail and keys on the counter. "It was Sammy's choice when or if she told you, not mine."

Their dad stepped into Dean's space and glared at him, a scowl pulling his lips down. "_She?_ You're going along with this bullshit, Dean?"

"Yes, sir, I am and it's not bullshit, sir. Sammy feels like a girl in her mind, if she wants to be that girl, I'll help her anyway I can."

Samantha couldn't help but smile through her tears at Dean's firm words, his chin tilted up and his eyes hard, unwilling to back down. The sight just made her love him even more than she already did.

Nobody spoke for a few seconds. She watched her brother and her father face off against each other, both of them stubborn as hell when they thought they were right. Samantha took a step forward when she saw her father ball his hands into fists, worried that he would hit Dean for his supposed insubordination. Finally, her father took a step back and blew out a puff of air.

"I don't have the time to deal with this nonsense. I have a hunt to get to." He stomped out of the room towards his bedroom, the sound of a drawer opening and then slamming closed again sounded after him. Walking back into the kitchen a minute later, he glared at both of them. "We'll be talking about this bullshit when I get back in a few weeks, boys."

He slammed the backdoor as he walked out, the truck's engine roaring to life and a moment later the squeal of tires marked his departure.

Dean pulled Samantha into his arms, wrapping her in his embrace as he nuzzled her neck. "Baby, you alright?"

Samantha let a sob fall from her lips as she shook her head no, burying her face into his chest as the tears began to flow freely after trying to keep them reigned in for so long.

"Don't listen to him, Sammy. It's not bullshit and if he can't accept it, it's his problem, not yours."

Dean let his hand slide down Samantha's spine to rest on the small of her back as he pulled her in closer, kissing her softly up and down her neck, trying to sooth her.

The sobs just kept on coming no matter how much she tried to make them stop. Her mind whirling on all the ways this could end and most of them weren't good. Would their father be able to accept Samantha like she was or was their family going to be torn apart by her wanting to live as a girl?


	2. Part Two

After that night the next few months were hell for Samantha. Whenever her father was there, which thankfully was even less than normal, they fought just as horribly, but twice as much. He thought she was confused and rebelling, yelling at her to forget about the 'girl' nonsense and fall back in line. He refused to accept that it wasn't a new thing or a way of rebelling against him no matter how many times she told him or in how many different ways.

Dean took her side through it all, unwilling to go against Samantha and her need to be who she was. His refusal to help their father convince her she was confused made the time when their father was there tense and uncomfortable for all of them.

Never one to back down, Samantha took to wearing her 'girl' clothes in the house full time. Most of the time he'd look at her and tell her to change back into her real clothes, other times he'd give her a sad and confused look that once or twice made her even plead with him to understand and try to accept it. Long after the fights had ended, one or both of them storming off, doors slamming in their wake, Dean would hold her in his arms while she cried herself to sleep, asking why he couldn't accept her like she was. He would murmur to her and tell her it would be alright, both of them ignoring the sliver of doubt in his voice every time he said the words.

Finally one night, their dad came home after being gone for a three week hunt and sat them all down in the kitchen.

"I stopped by Missouri's on my way to the hunt for help with the ritual," her father said quietly as he fiddled with the beer bottle in his hand. "She told me she knew what was going on and to get my head out of my ass and make it right."

Dean moved his hand under the table and gripped hers tightly, giving her support and strength.

"Missouri said she'd seen what your future is and that _'if you can't accept_ _Samantha Winchester and all she entails you'll lose them both forever.' _She told me I was a fool if I didn't listen to her."

Samantha felt Dean stiffen at his words as her body did the same. Did she know about them? Did she tell their father? He wasn't ready to hear about that change in their relationship as well as Samantha's gender issues and they weren't ready to tell him for risk of the fallout. She knew that whatever the future held for her, Dean would be right beside her as her brother and as the man she loved, but they were still young and she knew the world wouldn't see their love as anything but wrong and disgusting.

After a moment he looked Samantha in the eye and then Dean, his eyes glistening with unshed tears. "You're my boys… well, my children, and I love you. I don't understand it, probably never will, but I can accept it if that means you two are still with me."

"Before you go any farther I want to say that you don't know everything…" Samantha softly interrupted him, squeezing Dean's hand tight as she spoke. "… and that before you say you can accept me for me, I need to tell you that I want to start living as Samantha Winchester full time, in public the next time we move and that I want to start taking hormones to begin the change from male to female."

Her father sucked in a deep breath and closed his eyes for a moment. He gripped the bottle in his hand so tight that his knuckles turned white with the strain and then he blew the breath back out.

"I can still accept that, but I want to make a few rules with this new change." He waited until she nodded and then spoke again. "You changing your body will make people see you different and that means men will see you differently. I need to make sure you know how to protect yourself when Dean and I aren't with you. I've been thinking for a while that you needed to learn the family business and start training… now's as good a time as any I'm thinking."

Worrying her bottom lip, Samantha said, "Okay."

* * *

><p>Training to be a hunter was brutal. Dean and their father spent hours upon hours making Samantha spar with them, learning how to take a hit, how to hit back, how to duck and dive and all that other stuff. She would go to bed at the end of each night feeling like her body was nothing but one big bruise and wishing that the soreness and the ache would go away. She grew skilled with every weapon in the family's arsenal, but was very adept at knives and her father made her always keep a couple on her body after she proved skillful with them.<p>

She started gaining muscles that at first were a good thing. She liked the toned firmness of her abs and the slight curve to her biceps instead of spaghetti arms she'd had previously, but the more she trained the more her male body moved farther away from the way she wanted it to be.

"God, look at that, I'm starting to look like one of those bodybuilders. Not even my loosest clothing is hiding these anymore…" Samantha sighed as she looked at her body in the mirror.

She was wearing a pairing of pink boy-cut panties with little hearts on them and a matching bra. Before she started training if she didn't looking too closely at her body she could convince herself that it was female; the thin slight frame had made it easier to believe. But now with all the muscles she'd gained from training she just looked like a teenage boy in girls clothes… she hated it.

"Sammy, you don't look like a body builder," Dean laughed as he stepped behind her and wrapped his arms around her waist. "You look beautiful, baby."

"No I don't, I look like a boy in drag."

"Well, technically, you are a boy in drag."

Huffing, she slipped out of his arms and walked back into their bedroom and started dressing for school. "Yeah, but at least before I was so slim that it wasn't so noticeable. Now I can't hide the fact that I'm a male wearing girl clothes. I need to start taking hormones soon or I won't be able to look like a girl, no matter what I wear."

"Okay, then let's find a doctor to start you on hormones then."

Whirling around with a nervous smile, Samantha blurted out, "Really?"

"Yeah, it was gonna happen sooner or later, and now that Dad is somewhat okay with you being a girl… why wait? Unless you're not ready?"

"No, I'm ready; I've been ready for years now!" Giggling, she launched herself into Dean's arms, wrapping her legs around his waist and kissing him all over his face. "Thank you, thank you, thank you!"

Dean laughed and kissed her back. "Love you, baby." He murmured against her lips.

"Love you too," Samantha sighed, her breath mingling with his as she licked his bottom lip; nibbling the plump flesh with a soft moan. "Love you so much, Dean."

* * *

><p>As it turns out, a lot of doctors had a problem with her desire to start the process from male to female. Six doctors wouldn't even consider treating her, they recommended psychologists to treat her "mental illness" as one put it, the others thought she was just confused and needed a listening ear to work out her issues. Three were too uncomfortable to begin the process before she was 18, even with her father's consent. Four were willing to proceed, but required two years, or more, of counseling before starting the treatment.<p>

Samantha was frustrated by the fact that so many people believed that she was confused or 'mentally ill.' One doctor had implied that if she just waited long enough she would be alright with the body she was born in… that she was a _"young boy on the verge of manhood with a world of possibilities ahead of you; don't let insecurity lead you astray."_

She knew who she was and what she wanted, thank you very much! She'd known since she was eight years old that she was born in the wrong body. It made her mad that other people thought they knew what was best for her, despite her vehement assertion that she had been contemplating this for years since she realized what was wrong. They wouldn't change her mind. She may be young, but she still knew what was right for her.

After that last appointment she had even begun looking for alternate ways to begin hormone treatment on her own. She'd read online that many transsexuals have problems getting the initial process started, just like her, and had begun the hormone treatments themselves through less than reputable means. Dean had flat out refused after hearing that, saying that he didn't want to take a chance that something would go wrong and hurt Samantha.

Finally after a month of refusals or stipulations that would take years to complete before she began hormone replacement therapy, or HRT as it was known as, Dean stumbled upon a doctor who specialized in treating the LGBT community specifically and had experience with transgendered patients. The doctor required counseling sessions before and throughout the process, but was willing to proceed within the year.

So seven weeks after Dean and Samantha's conversation, she began HRT.

The first month or two Samantha didn't notice much of a change, maybe her nipples being a bit sore and itchy or a little less hair here or there, but nothing much. Then it seemed over night that she started noticing changes in her body. Her nipples grew larger and her chest began to grow minutely as she slowly filled out the training bras she had always worn without true need of them. The fat on her body began to shift as it redistributed to other places like her hips and thighs. Her face thinned out and she began taking on more of the delicate feminine features that she had envied on other girls for years now.

What made her giddy and excited though were the changes in her genitals. In the last four or five months she had begun entering into puberty. Her testes had begun to drop and heavy coarse public hair had begun to form around them and on her legs, arms and armpits. Samantha's unusually high voice had started to lower and she had irrationally feared that she had waited too long before beginning HRT. But when the changes from the hormones began, her testes stopped growing and even grew a little smaller. The hair that had begun to sprout in unsightly places thinned out or stopped growing all together, and her voice got a smooth feminine quality to it that had Dean's eyes glazing over in lust whenever she teased him with it.

Besides the fact that she was slowly making her way from a male to female body like she had longed for for so long, there were a few other perks to the HRT. Dean seemed to find the changes in her body beautiful and he spent hours in the bed at night cataloging the changes to it. His hands and lips, the weight of his body on top of hers; every look made her feel cherished and loved for who she was and what she'd be one day. It was something Samantha looked forward to each night, though sadly things never went past a certain point.

It had been a year since they had gotten together and though they had graduated to mutual orgasms, they hadn't gone all the way yet. Samantha had just turned fifteen the week before and, while she felt she was ready to go further, Dean held steadfast to the fact that he wanted to wait until she was sixteen. But just because they hadn't gone all the way yet, which Samantha looked forward to with bated breath, didn't mean that they didn't make up for it in other ways…

"Please, Dean?" Samantha pleaded, giving him the biggest puppy dog eyes she could, her bottom lip jutted out as she looked up at her brother who was laid out on top of her.

"I thought we decided to wait until you're sixteen?" Dean hedged, as if she had played any part in 'their' decision.

"Yeah, to go all the way, but I've been thinking about you fingering me," she breathed into his ear, her warm breath ghosting over him, making him shiver and give an involuntary thrust against her.

She would have smirked at the glazed look that fell over his eyes if she wasn't worried he would say no just to spite her. "Remember last week when you and Dad went on that hunt in Witchita overnight?"

"Yeah," he groaned as he nuzzled her neck, licking the fine sheen of sweat that had gathered in the unusually warm spring night.

"I fingered myself in our bed, thinking about you doing it… your thick fingers inside me, thrusting in and out as you sucked my nipples... they're so sensitive since I started HRT, can't stop thinking about how it will feel with you sucking them inside your mouth." A mewl slipped past her lips as Dean thrust down against her again, this time slamming into her body as his hands slipped underneath her body and gripped her ass.

Their groins slid against each other's, the sweat and pre-come giving just enough lubrication to allow their flesh to glide back and forth, the friction setting her body on fire. She tightened her legs around his waist, holding on as he pounded into her, wishing he was inside of her, filling her up and stretching her wide. "Please… please, please, PLEASE!"

Dean groaned and then scrambled over her body to reach the nightstand and grab the half used bottle of lube they kept on hand. He squirted a drop of lube on his fingers and threw the tube on the bed as Samantha wantonly spread her legs as wide she could. She glided a hand down her chest until the fingers brushed past a sensitive nipple, her moan filling the quiet room.

One of her brother's fingers lightly circled the furled muscle guarding her entrance, letting the lube slick the edges before he pressed the finger into the first knuckle. It wasn't large, but it was bigger than her own fingers and she sighed in bliss at the feeling of a part of Dean inside her for the first time.

"I can take another, Dean, give me another!"

She thrust her fingers through his short spiky blonde hair and gripped his scalp as he pushed another finger in along with the first, pushing them both in as far as he could go. Samantha gasped and rocked her hips upwards as he pressed against her prostate, a burst of pleasure unfolding within her.

She could feel Dean's warm breath against her hipbone, his lips kissing the flesh every time she thrust down onto his fingers. All she wanted was that hot wet mouth making its way up her body, licking and sucking and biting as it moved until those lips wrapped around her aching nipples and pulled the building orgasm from her body. She knew it would be explosive, his lips suckling her nipples, his fingers thrusting inside her… his dirty words taking her higher and higher.

Dean pulled his fingers out of her and then added a third, pressing repeatedly against her prostate as he thrust them in and out, in and out, in and out; her breath coming out shallow pants as he worked her over.

"God, so beautiful, baby girl," Dean groaned against her hip, "knew your pussy would be tight and wet for me. Just waiting for me to shove my fingers and dick in there and slam home. Can't wait 'til I can get in there and mark you as mine inside and out. Fill you full of my cum."

Samantha choked on a sob, Dean's voice and words sending spikes on painful pleasure coursing from her groin outwards. Just that husky growl of his, the way vowels rolled off his tongue like molasses, made her want to cream her panties on most days… now, with those filthy words and those skillful fingers working her body over, she was on the edge of oblivion and a second away from falling.

Dean slowly worked his way up her body, filthy dirty words spilling from his lips and staining her sweat slicked skin as he went. His tongue slid out from between his lips to flick around the curve of her belly button making her cry out in shock as it felt like the small little square inch bit of flesh was directly linked to her groin; sending pulse after pulse of pleasure spiking towards her core.

Her body tightened up as she felt the edge coming closer and closer. Samantha began babbling uncontrollably as his wet mouth finally covered one of her nipples, teeth scraping against the sensitive flesh before pulling the nub inside with a powerful suction that brought a scream from her lips as she exploded into tiny little pieces of pure sensation.

When she came to, Dean was slowly thrusting against her hip, his cock slick with pre-come as he grunted around her aching nipple. His eyes were on her face, filled with love and wonder and trust, as he came closer to orgasm. Samantha slipped a hand in between their bodies and wrapped it around his cock, his groan making her grin as she began sliding her hand up and down the length, gripping him tight as she brought him off.

"Love you, baby girl… look so perfect under me," Dean groaned as he flicked the tip of his tongue around her areola, smirking when she gasped at the pleasure/pain it elicited. "Can't wait to be inside you for real; your tight pussy wrapped around my cock as I pound inside you. Fuck!"

Pressing his face into her breasts, Dean gave a deep groan as he came, his cum spilling over her hand and onto her stomach, the warm wet semen a balm to her aching body. He slumped down onto her with another groan and then slid off a bit to make sure he wasn't squishing her. Dean was always looking out for her that way, even in a moment like this when he brain was short circuited on overwhelming pleasure.

Leaning over her again, Dean threaded a hand through her hair before cupping her cheek. He pressed his lips against hers, their breaths mingling before he coaxed her lips open and slid his tongue inside. Lifting her arms up, Samantha wrapped them around his neck and kissed him back with all the emotion she had inside her before sleep finally pulled her under.

* * *

><p>Four months after she began taking hormones, they moved again. Using a contact he had through hunting, their father had Samantha's records hacked, including her birth certificate, and altered them so that she was now listed as Samantha Winchester, female.<p>

She'd hugged her daddy so hard when he'd told her, with a blush on his face. That night she had made a big dinner with all the fixings. They spent hours at the kitchen table laughing and joking, a true family for what felt like the first time in a very long time. Just the memory of it made her all warm and happy inside.

"Sammy, you ready yet?" Dean yelled from the living room of their new apartment.

Samantha could hear him grumbling about being late for work if she didn't hurry her pretty ass up. Her eyes bouncing back and forth between the two outfits laid out on the bed, Samantha bit her lip as she tried to choose which one to wear.

It was her first day at the high school and her first day ever as Samantha Winchester in public. Up until then she had been nervous about being herself out in public. There was no doubt that she was comfortable with herself and her choices, but she worried that people would find out and judge her… make fun of her. She was a girl in her heart and mind but to everyone else, besides her brother and father, she would be just some weirdo boy who liked to dress up in girls' clothes and who'd started to grow breasts.

This was a big step and, though she was sure it was the right one, taking that step was the hardest thing she'd done since she'd confessed to Dean and then their father about her transsexualism. She was doing this, she'd made up her mind, but she had to look perfect… like a proper lady; a _real_ lady.

Blowing out a puff of air to get a strand of hair out of her eyes she closed her eyes and said a quick _'__eeny meeny miny moe__'_ and then hurriedly to pulled on the winning outfit. Running to the bathroom she made sure her hair and makeup were still in place and then walked into the living room.

Dean stared at her for a full minute, his eyes roaming lustfully over the pink knitted sleeveless sundress that showed a hint of her every growing breasts and the white cardigan over it. She had on a pair of strappy white sandals and a few multi-colored bangles on her wrists. Samantha's hair was in long loose wavy curls that had grown quite a bit over the last few months and brushed just passed her shoulder blades.

She felt like a million dollars through Dean's eyes and she couldn't help but giggle in glee. "So what do you think? Do I look like a lady?"

"Baby, you look perfect." Dean said softly as he walked up to her and wrapped his arms around her tiny waist and pulled her close. "I'm gonna have to beat all the boys at your school off you, you look so good."

Laughing, Samantha grabbed her messenger bag from the couch and then said quietly, "Okay, I'm ready."

Dean looked at her a moment. "You sure? We can wait a while, screw the school."

Lifting up her chin in and giving him a determined look she nodded. "No… I'm as ready as I'll ever be."

"That's my girl."

Ten minutes later, walking up the steps of the high school, Samantha took one last look at Dean for courage. He stood leaning against the driver's side door grinning at her, shooing her forward like a mother hen. Smiling back at him, she walked through the entrance and made her way to the school's front office.

A woman that looked like she had a pound of makeup on her face, artfully applied with a paint brush, stood behind the counter at the office. As Samantha stepped up to the counter, one of the woman's painted eyebrows rose, "Can I help you, missy?"

"Um… I'm a new student. It's my first day."

"You must be Samantha." She grabbed a sheet of paper from a file and handed to her.

"Here's your schedule with a map of the school, as well as school policies to abide by. If you have any questions please feel free to come back and we can answer them for you."

Nodding, Samantha noticed the time on the clock over the woman's head and then said thank you before hurrying to her first class. She made it just as the bell rang and she took the last open desk in the very back.

The teacher read from a sheet on the table, calling out student names, making a checkmark as each student answered. After a minute he called out, "Samantha Winchester?"

Raising her hand, Samantha looked said, "Present."

"Hey, you must be new! I'm Marnie." She heard a chipper voice from beside her.

Turning her head, Samantha smiled at the girl in the desk next to her. Marnie was dressed in a black ruffled skirt with purple leggings and a striped black and white shirt. Her hair was black streaked with gray and red and just from the first look Samantha could see at least six piercings and a layer of dark heavy makeup on the girl's eyes and lips. She wasn't normally the kind of person Samantha made friends with, Marnie was obviously an extrovert, something worlds away from Samantha. Of course, it wasn't like she made a lot of friends anyways. Usually she kept to herself, but occasionally she formed a friendship with a fellow geek. However, Marnie had a welcoming smile and a curious interest on her face that made Samantha feel like she could be a good friend, for however long they were in the town at least.

"Hey, I'm Samantha. Nice to meet you."

Introducing herself to Marnie as 'Samantha' felt like the first truly genuine thing she'd ever said to anyone besides her brother and father, and it felt wonderful.


	3. Part Three

Samantha's sixteenth birthday came along before she knew it and passed just as quickly. The last six months they had bounced around from one state to another so many times Samantha was feeling whiplash from it and she'd gone to seven different schools since she'd started showing the public the real Samantha. She had met a few good friends along the way and had found it hard to leave the budding friendships she'd started, but she'd always had the most important person in her life right there beside her through it all, making things better with just a teasing smirk and a loving kiss.

Three weeks ago they had settled into an old double-wide trailer on the outskirts of a small town on the border of Kansas and Oklahoma. It was falling apart, having seen it's heyday probably around what felt like the turn of the century, but it was better than most of the skeazy motels they had stayed in over the years, so that was something.

Their dad was away again on a hunt, big surprise there, and they had the place to themselves. They were taking advantage of knowing they were truly alone with dad a state away for the first time in a month. Making out with Dean was always a favorite past-time of Samantha's; her brother lips against hers, enjoying the simple pleasure of kissing for kissing's sake. But Samantha was on a mission and was determined to get her way this time.

"You promised." Samantha whispered. "Don't you want me?"

A strangled laugh erupted from Dean as he pressed Samantha onto her back and crawled on top of her, his eyes roving over the small red scrap of lingerie that covered his girl. He settled his body in between her thighs, fitting perfectly between them like she were made only for him. "Baby, that's not it. I want you so much that sometimes it feels like I'm dying if you're not in my arms. I can't stop dreaming about what it will feel like being inside you, hearing you scream my name as you cum… the way you'll clench tight around my cock and milk me. There's _nothing_ in this world I want more than to be inside of you. I just want to make sure we do it right and that it's something that you won't regret later on."

Rolling her eyes, Samantha flipped Dean onto his back and straddled his lap as she glared down at him, angry fire flashing in her eyes.

"Dean, I love you, you _idiot_ and _I am ready._ I've been ready for a while now and there's no way I would regret this. You don't think that I've dreamed about it too?" Samantha pressed her bottom down against the hard length of his cock, undulating against it with a smirk on her lips as Dean groaned, his hands clenching around her hips. "I wake up panting from dreams where you hold me down and pound me into the mattress. I feel empty… wanting you inside me… I want to know what it feels like to have your dick stretching me open and you cumming inside me. God, I want it so _bad_," she moaned.

"I just don't want you to regret this," Dean sighed, looking up at her with concerned eyes. "This is your first time, baby, and it needs to be special."

"You don't think this is special?" She asked. "I'm officially sixteen now and we've waited for two years. We've got the house to ourselves; Dad won't be back for at least a week. I bought pretty new sheets and this gorgeous teddy. I did my makeup and hair special for you and laid out candles… and we love each other. What could be more special than that?"

Giving her brother the biggest puppy dog eyes known to man, Samantha leaned down and ghosted her breath over Dean's lips, her breasts pressed heavily against his bare chest. "Please…" she begged softly, her voice taking on a low husky tone.

Dean's pupils widened and his breath came out in heavy pants, his dick going from half-hard to rock-hard in a second flat. '_Score one for my womanly wiles',_ Samantha thought, suppressing the giggle that wanted to break free. Samantha had a second to think on her burgeoning 'womanly wiles' before Dean surged up and flipped her over onto her back with a low growl. She gasped, taken a little by surprise and a lot whole lot of lust.

"Sammy, god, baby, so fucking beautiful," Dean moaned as he nuzzled down her body, his lips traveling a familiar path… but this time it would end in a place that they'd both been dreaming of for so long. "Gonna make you scream and moan my name… eat you out until you can't take anymore and then I'm gonna fuck you over and over; make you cum on just my cock, nothing else!"

Samantha whimpered, her mind a puddle of mush and her body on fire. She knew he could do everything he'd said and more. Dean's mouth brushed up against a hard nipple, the warmth of his breath muted by the thin sheer red lace covering it. Not even thirty minutes ago she'd nearly creamed her panties as she looked at herself in the mirror and thought of what Dean would do to her in the sheer teddy and loving the way her body looked so womanly in the lingerie… but now she hated it, hated the fact that it separated her from Dean's mouth, his lips, his tongue, his teeth. She wanted to rip the scrap of material off, without a care for the money she'd scrimped and saved for months to buy it; all she wanted was that hot wet mouth to engulf her and never let go.

Dean was of the same mind, maybe a little more careful than she would have been, as he pulled the teddy off her body with a feverish gleam in his eye. Swooping down, his mouth took one of the hard nubs in his mouth, his teeth biting down on the flesh, making her cry out as sensation overtook her.

"_Dean_!" She screamed as pleasure sparked through her body and down to her groin, lighting her body on fire. She wrapped her arms and legs around him, her thighs clenching around his waist and squeezing tightly as she whimpered at the feel of his hard dick pressing up against her bottom, wishing that he could just slam home inside her. "I… oh god… please…"

"I know, Baby. I'm gonna take you care of you, make you scream my name a couple of times before I take you." Dean grinned up at her from around the hard nub between his lips, letting his tongue circle the hard flesh and enjoying the moan that slipped from his girl's lips.

Dean turned his attention back to Samantha's breasts, closing his eyes and sucking and laving the nipple with a fevered determination. Samantha whimpered and moaned, squirming under the assault from his mouth as he his teeth grazed the side, biting down softly around it and pulling slightly. It was pleasure and torture and heaven all combined.

Ever since she had started the hormone treatment, her breasts had been sensitive, always verging on the precipice between pleasure and pain. Dean had noticed it from the very beginning and hadn't wasted a chance since to make her cum from just his mouth and hands on her nipples.

One of Dean's hands cupped her other breast, squeezing and massaging the flesh; letting his thumb graze back and forth, back and forth, across the nipple… a startling change in sensation from the harsh bites and sucks being administered to the other. Gripping the sheets in her fists, Samantha closed her eyes and let the pleasure overwhelm her.

"_Dean… yes!"_ She clenched her thighs around his waist, pressing herself as close to him as she could get as she grew closer and closer to orgasm.

Samantha felt her body tightening, her moans becoming a pitiful string of pleas for Dean to stop and keep on going at the same time. She gripped his head, her fingers holding on tight to his hair as her body stiffened and she screamed his name as she came.

"So damn beautiful," Dean whispered as he nuzzled her breasts, giving sweet little kisses here and there as he slowly moved his way up her body.

Opening her eyes, Samantha smiled at Dean up above her and grinned as he kept on moving over her, his body straddling her chest.

"Open up, baby girl," Dean murmured as he pressed the tip of his cock against her lips, seeking entrance inside.

Opening her mouth, Samantha sucked the head into her mouth and groaned at the tangy flavor of Dean that she knew so well. Swirling her tongue around his cock, Samantha began bobbing her head up and down, taking more and more of his length with each pass. The whole time she kept her eyes on him, watching as he looked down at her and groaned, his hips giving involuntary thrusts every so often.

Gripping Dean's hips, she pushed them down against her face a couple of times, letting Dean know what she wanted and he caught on quickly. Dean pressed his hands palm down against the wall in front of him and began thrusting inside her mouth, his cock hitting the back of her throat every time.

Samantha moaned around the thick length, loving the feel of how Dean just shoved his cock down her throat, his eyes glazed over with lust as he stared down at her.

"That's it, baby, just take it" he groaned with a deep shove, "… just take what I give you, Sammy. Such a perfect little cocksucker; my little cocksucker. Baby girl you're so perfect..."

She sucked harder as her brother's words hit her ears, the dirtiness of them making her squirm and moan because they were true. She was his, always had been, she'd take anything and everything he gave her and always want more.

Dean started pounding down into her mouth, his cock choking her and making it hard to breath, but she loved it. Even with tears streaming down her cheeks, she gripped him even tighter and silently begged for more, sucking for all she was worth as his balls started tightening up towards his body as he came closer to coming. Pulling back so that just the head of his cock was inside her mouth, Samantha had just enough time to create a little more suction before Dean came down her throat, big globs of spunk filling her mouth and flowing down into her belly.

Dean's groan filled the quiet room as he shook above her, spilling every drop he had inside of her mouth. After a few moments he crawled back down her body and breathed into her chest, his eyes on her the whole time. Samantha grinned at him, sweat and small drops of cum dribbling down her chin. She wiped the cum off her chin and sucked the fingers into her mouth, savoring the flavor a little bit more.

Dean laughed. "Damn, that mouth of yours is something else, baby girl. Needs to be licensed as a lethal weapon… able to make any man a puddle of goo at any moment."

A giggle spilled out from her lips as she wrapped her arms around Dean's back and held on tight. "Only for you though."

"Damn straight!"

They laid there for a while just enjoying the moment before Dean lifted his head as she began squirming under him. Sucking him off had just made her excited about the big finish and she was ready to go again.

Smirking down at her, Dean began kissing a trail down her body, eliciting moans and whimpers as he paid attention to all the special places he knew would make her melt. Samantha felt Dean lean over the edge of the bed and grab the new tube of lube on the night stand, the sound of the cap opening causing an excited squeak to slip past her lips. Dean laughed lowly and positioned himself on his stomach between her spread legs, his breath ghosting wonderfully over her thighs as he breathed.

Samantha gasped at the cold feel of his lubed finger circling her hole before their body temperatures warmed it up. She could hear Dean's soft laugh as he began pushing the finger inside her, the finger sliding inside to the hilt without any trouble. Dean had been fingering her for a year now and her body was used to the feel of Dean's fingers inside of her.

Leaning down, Dean nuzzled into her inner thigh, nipping the delicate flesh lightly as he thrust his finger in and out of her. Samantha mewed and spread her legs wantonly as she gripped Dean's head, her fingers carding through his hair as she gasped and squirmed at the feel.

"Oh god, Dean… another please, I'm ready!"

Dean quickly pulled out the finger and then shoved two back inside, Samantha's hips shooting off of the bed as he pressed against her prostate and fondled the ball of nerves. Samantha cried out, mumbling nonsense as he worked the fingers in and out, shoving roughly just like he knew she liked and bringing her to peak quickly and then backing off before she tumbled over.

"Sammy, baby, you're so hot like this. My fingers inside of you getting you wet and ready for me," Dean groaned as he nipped her hip and licked the head of her penis with a smirk.

It was odd how much she enjoyed the feel of him licking the head, she often ignored the glaring proof of her wrong gender from day to day, but Dean never did. He told her that as long as she had it, it was a part of her, even if an unwanted part and he was going love it and use it to make her cum until it was gone. When he said things like that Samantha was always amazed that he was really hers, that she'd found someone who knew about every little part of her mind and body, and loved it all unconditionally.

A gasp erupted from Samantha as she was pulled from her thoughts, Dean shoving three fingers inside of her without pause. The stretch and burn of it, made her clench her hands around Dean's head, a low throaty moan filling the room as he thrust back and forth inside her body.

"Okay, I'm ready, Dean… get inside me," Samantha gritted as she thrust down onto those amazing fingers, trying to get them farther inside of her then they had ever gone before, "… please, Dean."

"It's alright, baby girl," Dean soothed as he pulled his fingers from her body and crawled up the length of her until his hips were cradled between her thighs, his cock pressing insistently at her opening. "I'm gonna go slow. Tell me if it hurts, okay?"

Samantha nodded as she wrapped her arms around Dean's neck and waited for him to push inside of her for the first time. She felt the head press firmly against the furled muscle of her hole just before it broke through the entrance and probed inside. The stretch and burn of him pushing inside her felt strange and wonderful at the same time and she couldn't believe that it was finally happening. She'd been dreaming about this for years and finally, _**finally**_, he was inside her after so long.

"Dean," Samantha sighed, pulling her brother down further, wanting his weight completely on top of her and holding her down.

"I'm here, baby," Dean murmured as he pressed in further, his hands flat against the bed on either side of her head to keep his upper body from crushing her. "Sammy, god, you're pussy's so tight."

Groaning, Dean leaned down and coaxed Samantha's lips open, sliding his tongue inside her mouth and twisting it around hers, their tongues dancing against each other as Dean continued to slowly push farther and farther inside her. Samantha gasped as he bottomed out inside her, the strange fullness felt oddly right and she wanted to take more, take every part of him inside her until they weren't two people anymore… just one entity, one being.

Flexing her hips, Samantha tried to get Dean to start moving, but she cried out as a sharp sting flared inside her taking her by surprise.

"Don't move, baby girl… you have to get used to me being inside you before I start moving, okay?"

Samantha nodded and tried to make her body relax around him.

"You know I love you, Sammy-girl," Dean whispered against her lips as he ran his hands down her body, tweaking her nipples with a practiced flick of his fingers.

Gasping, she couldn't speak as a spasm of pleasure/pain spiked throughout her body, she clenched down around Dean's cock inside her. Dean groaned at that and gave an involuntary shallow thrust, his hands slipping underneath her body to cup her bottom and lift her lower half up for a better angle.

"I'm ready… please say I'm ready." Samantha whimpered as she clutched around Dean and flexed her hips again, another gasp falling from her lips as Dean's cockhead hit her prostate perfectly.

"Good enough," Dean growled and pulled almost all the way out.

Gripping her bottom tightly, Dean slammed back home inside her and Samantha saw stars. The pleasure was like nothing she'd ever known before and instantly became her new obsession, it felt so good. "_Dean_!"

"Yeah, baby girl," Dean growled as he pounded in and out of her, slowly getting a rhythm going inside of her "… take it, take what I give you, baby!"

"Ugh, yes!"

"So pretty, Sammy… all mine, always been mine, since Dad put you in my arms," his rhythm grew faster as he thrust, his hands holding her so tight that she'd probably have bruises in the morning. "You'll always be my baby girl, my Sammy!"

Clenching her legs around Dean's waist, Samantha held on as Dean pounded down into her, the feel of him moving inside of her quickly taking her higher and higher with each thrust. This had to be heaven… nothing else would ever feel so good again; Dean inside her, around her and telling her she was his.

Slipping a hand between their bodies, Dean pinched one of her nipples and Samantha exploded into a million tiny little pieces, her body stiffening as she came. "Dean!" Samantha screamed, the sound bursting from her lips as she clenched around him, sending him tumbling over the edge, cumming inside of her. The warmth of his cum filling her was everything she'd thought it would be and more; marking and claiming her like no one else ever would.

Dean slumped down onto her, his head resting on her pillowed chest and his warm breath making her shiver as it met her sweat dampened skin. Dean nuzzled her breasts, licking the wet skin with a quiet groan, his softening cock finally slipping out of her as a trickle of his cum quickly followed. The sensation of it dripping out of her hole felt deliciously obscene and she loved it.

One of Dean's hands slipped down between their bodies and circled her wet dripping hole, pushing in slightly as a squelching sound filled their bedroom. He pulled back a little to look at the sight, his breath hitching, and Samantha grinned.

"Pretty little pussy, leaking my cum," Dean whispered as he crawled down her body and settled between her thighs, face pressed close to her groin.

Samantha gasped as she felt Dean's tongue lap at her hole, licking away the slowly dribbling cum as it leaked out of her body, his moans and slurps filling the quiet room. She closed her eyes and squirmed under the assault, her body tingling with a slowly building renewed interest and need. Allowing her fingers to thread through Dean's hair, Samantha laid back and just enjoyed Dean's undivided attention for as long as she could.

Finally, Dean wandered up her body and sighed against her breast before lifting his head and looking up at her. "Goddamn, baby girl, so beautiful… No regrets?"

"Not a one, Dean… it was perfect." Samantha laughed as she threaded her fingers through his hair and gently pressed his head back down onto her breast and closing her eyes, enjoying the afterglow of her official first time with Dean. "Love you, Dean."

"Love you too, baby girl."


	4. Part Four

After Samantha started her senior year of high school, the school's counselor had met with her to begin the process of applying for college. Samantha's GPA was 3.98 and she had a long list of extracurricular activities that colleges looked for, she was almost assured a full ride with that and her father's low income.

For months afterward she had kept quiet, unsure how to broach the issue with her brother. She knew that Dean loved her and that he would do anything for her, but he also felt the same way about their dad. She worried about what would happen if their dad didn't like it, that Dean might have to choose between the two of them. It was the same kind of fear as when she told her father about her gender issues all over again, the fear of losing Dean and everything that mattered to her because of her need to life a different life.

Finally, after months of worrying and aborted conversations, Samantha put on her big girl panties and told Dean.

"I want to go to college, Dean, and I want you to come with me," Samantha whispered quietly as she snuggled closer to him under the warm covers of their bed. Snow was falling heavily outside the bedrooms window, the flurry of wind and snow from the storm nearly overpowering her whisper. "My counselor said my grades are excellent and that she's sure I'll get a full ride…"

"I know, baby… I've been trying to ease Dad into it, but he's not exactly easy to talk to." Dean sighed pulling her close, his large hand rubbing up and down her back under the tank top. "Was thinking that we could convince him to move us wherever you get accepted, make that our home base. Me and him could still go on hunts, we'd just keep the hunts within the bordering states and come home after each one."

"You think he'll go for it?"

Dean stayed quieted for a while and then answered. "I don't know, Sammy… we'll see when we tell him."

"If he doesn't, what will-" Samantha whispered, her throat closing up before she could finish the question.

She knew Dean loved her, but this was their dad and Dean had always been a good soldier who followed orders. Samantha wasn't sure what side he would chose, or even if he could pick a side. Her heart clenched as she thought about her family falling apart… of possibly losing Dean or their father.

She had always hated the hunting life; moving from one run down house to a rundown roach motel, then to a different place all over again. She'd gone to 26 schools since she started the first grade and had to leave behind the few friends she'd made all along the way. She was ready for a normal life, for having one place to call home… for it to be filled with things she loved. That meant something to her; for it to be a home, not just another place that they lived in.

Dean didn't talk about it often, but she knew he felt the same way. Even though he was torn by the sense of duty he felt to their father, for the hunt for the demon who killed their mother, every once in a while he'd get this wishful longing look in his eyes when he saw a happy family cross his path. Whenever she saw that look on his face Samantha always got so angry with their father for dragging them along on his unending quest for vengeance… angry with the demon that killed their mother and took the promise of a bright happy future away from them all.

Some of the happiest moments she could remember in her life were the times when it was just her and Dean by themselves. Living in some dilapidated house their father had found for them while he went off on a string of hunts for months at a time, Dean working at a local repair shop to support them while Samantha went to school and took care of the house and feeding them. Those moments weren't anything special for the average person, but for her, they had been a few bright shining months of sun and happiness in a long string of dreary years.

Settling over her, his body cradled between the spread of her thighs, Dean cupped her cheek and stared fiercely into her eyes. "If he can't accept what we're offering, then it's his loss, baby. It's you and me. Always… if he doesn't agree then we pack our shit and go. I know how much this means to you, Sammy, I'm not gonna let him ruin this. Okay?"

"Okay." She smiled up at him as she carded her fingers through his hair.

"So where'd you apply and which one do you want the most?" Dean asked as he rested his head on her breasts, a hand cupping the side of one of them, his lips absently brushing over the slowly hardening nub.

"I applied to Harvard, Dartmouth, Yale and Stanford… but I want Stanford." She grinned, stars in her eyes as she spoke. "Can you imagine it? Us in sunny California, no snow storm in sight… You in a mechanic shop tinkering under the hood of classic muscle cars, me going to school to become a lawyer who specializes in LGBT cases."

Chuckling Dean nodded his head, his lips brushing up against a nipple as he moved. "Yeah, baby, sounds perfect."

"Yeah it does, doesn't it," Samantha hmm'ed and then gasped as Dean's lips brushed up against her nipple, this time she was sure on purpose. "Okay, I'm done talking now…" she sighed as she arched her back and pressed her nipple against Dean's wandering lips.

With a smirk, Dean latched his lips around the hard nub and sucked it for all he was worth as his hands began to wander down her body…

John slowly pulled his truck into the driveway of the small cottage he'd rented for them for the last three months, a tired sigh falling from his lips as he parked. He'd been away from a few weeks; a string of hunts had followed one after the other since he left for the hunt in Tennessee three weeks back. Pulling his duffle from the cab, John checked the mail box before heading towards the house. Absently, he sifted through the mail, ignoring the junk mail and keeping the credit card offer for a later perusal, John stopped from one step to the next as his eyes landed on the last bit of mail in the pile. Looking at the letter in front of him, he froze for a moment, confusion warring with annoyance and frustration at his youngest child. Embossed across upper portion of the thick manila envelope in bright red was "Stanford University." The name and the weight of the large envelope told him all he needed to know.

His son, dammit, his _daughter_, he shook his head as even after four years he still had trouble remembering that his son Samuel was now Samantha. '_**My Sammy**_' he finally lands on, had gone behind his back and applied to college when he told her no. There were so many things wrong with the picture in front of him, like the fact that Samantha disobeyed him or that she wanted to go off where she'd be alone and unprotected or that she was giving up on helping their family find the demon who killed her mother.

He was angry, no, he was pissed… she had always rebelled against him. Whenever he said to go right, she'd go left just to spite him. Samantha was stubborn and disobedient, a liability when he needed a soldier who would just listen and do what they were told. Her constant whining that she wanted a 'normal' life; that she wanted to stay at the school even though their hunt was moving on. Since she was a baby she had always bucked against his orders and he was tired of it. He was finally going to make it crystal clear that her days of youthful rebellion were at an end.

Stomping into the house, he dropped his duffle onto the kitchen table and made his way through the current hovel of they called home sweet home until he reached his kids' bedroom door. Clenching his hands into fists and blowing out a puff of hot air to try and calm himself, he opened the door and choked on the words he was about to yell.

His babies were curled up together on Dean's bed, naked as the day they were born. Samantha was laying half on top of Dean, her arm wrapped around his waist and her hand resting just below his navel. Dean had an arm around her as well; the hand attached cupping her ass possessively as he slept. The smell of sex and sweat and lube was still in the air and he gagged as he registered it in his mind.

'**They're fucking!'** he couldn't help but scream in his mind.

"WHAT. THE. FUCK?" He bellowed as he barged into the room, waking them from their dreams.

Dean's eyes bulged as he saw him standing over the bed, fists clenched and his nostrils flaring as the rage consumed him. "Dad... I can explain!"

"Explain what? That you're fucking your brother?" Something in the back of his mind tells him that 'brother' isn't the right term anymore, but he ignored it, his anger stomping the thought down before he could feel guilty about it. "What the hell is wrong with you two?"

Samantha was holding the sheet up against her chest, tears falling from her eyes as she looked up at John with hurt, anger and dread. John wanted to comfort her, but he wanted to shake her as well. Why the hell would she let her brother touch her like that?

He'd always known that they were closer than most siblings, he'd figured that was just the way it was for them… living their life on the road, bouncing from one place to another, nobody and nothing a constant in their lives except for each other. John had seen the way they cuddled together on the couch, or the way that even at their ages they still ended up in the same bed more often than not. His mind had gone there a time or two, a fleeting thought that maybe they were too close before he'd laugh at himself and think he was too paranoid… that there wasn't anything like that going on behind his back. Now he wished he'd listened to that voice that whispered something was wrong over the years.

"Daddy," Samantha says through a hiccupping sob, "we love each other."

"You're brothers! It's disgusting and perverted… this isn't right, I won't allow it!" Gritting his teeth he scowled down at his children. "Get dressed… right now! We're gonna talk about what is acceptable and what isn't and about _**this!**_" he barked out as he threw the Stanford acceptance letter on the bed beside them, Samantha's eyes widening as a gasp slipped from her lips, "And then we're never having this conversation again, am I clear? And so help me god, if I ever find out that you've touched each other again…"

"No, sir. I'm sorry, but we love each other and you don't get to decide how we live our lives. Not anymore." Dean said quietly as he stood up from the bed, not a lick of shame for his naked body. His son's chin was jutted out in anger, his eyes blazing as he stared John down.

"What did you just say to me, solider?"

"I said, no, sir."

"This how it's gonna be?"

He was quiet for a moment, his face unreadable and then he nodded his head. "Yes, sir."

"You feel the same way?"

Samantha wrapped the sheet around her body and crawled over the bed to stand beside her brother, their hands clasping each other's. "Yes, sir."

"Fine, get out."

"What?" Samantha gasped as her eyes grew impossibly wide.

"I said get the fuck out and don't come back. No children of mine are going to live a perverted life like this." Before he could regret the words he stomped out of their room and into his, slamming the door behind him.

Through the thin walls John could hear Samantha's sobs and Dean murmuring to her. For a few minutes that was all he could hear before the sound of drawers opening and closing filled the silence. The ping of clothes being quickly pulled off of hangers sounded like gun shots, covering up the breaths he forced in and out of his body. John leaned against his door, his eyes closed as he listened to the sounds of his children leaving him forever.

Thirty minutes after they started packing, they finished loading the Impala with their meager possessions. John watched them through his bedroom window, the light in his room off, concealing him from his children.

"It'll be alright, Sammy. I told you… it's you and me, baby, always." Dean said softly as he wrapped his arms around his sister's waist, holding her tight as her sobs echoed into the quiet night.

The bitter taste of regret formed on his tongue as he watched them comfort each other. As soon as he'd said the words, disowning them, he'd regretted it. They were his children and he loved them, even if they were together like… _that_… but his stubborn pride wouldn't let him take everything back now.

The memory of Missouri's words of warning said years ago floated through his mind, _'if you can't accept_ _Samantha Winchester and __**all**__ she entails you'll lose them both forever.' _He wondered if she saw this in her vision. He wondered how much she was cursing his stubborn pride at that very second and he was shamed by even the thought of it.

"Come on, Sammy, it's a long drive to California."

Grabbing the last of their bags from the front steps, Dean took Samantha's hand, threading their fingers together without thought in an intimacy that spoke volumes, Dean lead them to the Impala. He open Samantha's door for her whispering something so quietly that John couldn't make out. Samantha smiled through her tears and leaned up to kiss him, whispering back, and then got in the car.

Dean rounded the car, his eyes landing on John's window with a sad, but determined look. Slamming the driver's side door closed, the Impala's engine purred to life a second later and then John watched as the taillights faded into the night, taking his children with them.

_God, what had he done?_

* * *

><p>The purring rumble of the Impala's engine filled the silence for a while, Samantha tucked tightly into Dean's side as they drove down the highway. Her tears had stopped a while back, the hiccups a few minutes later, her face slowly taking on a resolved look that made Dean equal parts sad and happy. He hated that their father had done this, made them choose, but if Dean had to choose it would always be Sammy… every time, no question.<p>

She was his world, everything he loved about it shown through her eyes and he wouldn't give her up for anything, not even their father.

"it'll be alright, baby, you'll see. We'll get a nice place in California, you'll go to Stanford and become a lawyer, I'll find a garage to work at and we'll be happy. Just wait and see." Dean murmured quietly against Samantha's temple, pulling her in close to him.

His baby girl, looked up at him, watery smile shining on her face and she nodded. "I know, I just wish he could be there with us, is all."

Kissing her temple, Dean whispered, "Maybe one day, baby, maybe one day."

Dean pushed a tape into the cassette player, the sound of their childhood starting up a second later. Eyes back on the road, Dean drove them towards their future holding his world close in his arms, humming quietly along with Kansas' _Carry on my Wayward Son_.

The end.

* * *

><p><strong>Author's Note:<strong> This series is a work of love for me as I have absolutely fallen in love with Samantha and Dean's story, so you'll be sure to have more to read in the very near future. I've already written two other ficlets in this verse and I plan to write more about Samantha and Dean's time at Stanford and their life together. Let me know what you think, feedback is love people, so get to it! *g*


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